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The document discusses the stereochemistry of natural products, defining stereochemical isomers and their significance in biological activity. It highlights the importance of chirality, optical activity, and enzyme catalysis in the biosynthesis of natural compounds like menthol. The conclusion emphasizes the role of stereochemistry in drug design and understanding biochemical processes.

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8 views

Natural Pre

The document discusses the stereochemistry of natural products, defining stereochemical isomers and their significance in biological activity. It highlights the importance of chirality, optical activity, and enzyme catalysis in the biosynthesis of natural compounds like menthol. The conclusion emphasizes the role of stereochemistry in drug design and understanding biochemical processes.

Uploaded by

josephazalete
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© © All Rights Reserved
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STEREOCHEMISTRY OF

NATURAL PRODUCTS

.
STEREOCHEMICAL ISOMERS

Stereochemical isomers are molecules, which have the same chemical


formula and bond connectivity but different relative arrangement in
three dimensional space. It is also known as
3D chemistry.
NATURAL PRODUCTS
Natural product is a chemical compound or substance produced
by a living organism, that is found in nature.
In the broadest sense, natural products include any substance
produced by life.

Natural products can also be prepared by chemical synthesis and


have played a central role in the development of the field of
organic chemistry by providing challenging synthetic targets.

The term natural product has also been extended for commercial
purposes to refer to cosmetics, dietary supplements, and foods
produced from natural sources without added artificial
ingredients.
CATEGORIES OF NATURAL PRODUCTS

Natural Product
(secondary metabolites)

Phenolic
Terpenoi Alkaloid
Steroids compou
ds s
nds

Menthol Caffeine Cholesterol Phenols


CHIRALITY
They are non-superimposable mirror images of
each other. Achiral objects, on the other hand, are
easily superimposable on each other.

Each chiral carbon must have four different groups. For


example, cholesterol have eight chiral centers.

Cholesterol
OPTICAL ACTIVITY

Each enantiomer of a chiral structure


reacts differently with polarized light.

Here in this example, (-)carvone has an


angle of rotation of -72°, (+)carvone one
of +72 °.
Enantiomer
If a molecule is non-superimposable on its
mirror image, then the molecule is said to have
enantiomeric relationship with its mirror image
molecule.
Terpene
Linalool has two enantiomeric
forms which are both found in
nature.
(R)-(-)-linalool enantiomer is
responsible for the fragrant scent
in lavender and sweet basil.
The (S)-(+)-linalool enantiomer is
largely found in essential oils of
coriander seed and sweet orange
BIOSYNTHETIC PATHWAY AND ENZYME
CATALYSIS

Biosynthetic pathways refer to the series of chemical reactions that occur within
living organisms to produce biomolecules. The steps could include Anabolic and
Catabolic pathways. Examples include Glycolysis, Amino acid synthesis, and
Terpenoid synthesis. They are enhanced by Enzyme Catalysis.

Enzyme catalysis is the process by which enzymes speed up chemical reactions


in living organisms. It also introduces or alters the stereochemistry of a
compound.
.Enzymes can be said to have a high stereospecificity because of ;
• Active site shape and chemistry
• Substrate binding: Enzymes bind substrates with high affinity,
positioning them for reaction. This binding is often stereospecific,
with the enzyme recognizing specific functional groups or molecular
shapes.
• Conformational changes
• Transition state stabilization
BIOSYNTHETIC PATHWAY OF MENTHOL
• The biosynthesis of (-)-
Menthol from primary
metabolism requires eight
enzymatic steps.

IUPAC name (1R,2S,5R)-


2-isopropyl-5-
methylcyclohexanol. A
terpenoid natural product
produced by many plant
species.

IPP- Isopentenyl
pyrophosphate
DMAPP- Dimethylallyl
pyrophosphate
IMPORTANCE OF
STEREOCHEMISTRY
IN BIOLOGICAL
ACTIVITY
• Enzyme Interaction
• Receptor Binding

(limonene) the compound which gives


different taste to lemon and orange are
examples of stereochemical isomers.
Thalidomide exists in two mirror-image forms: it is a racemic mixture of (R)-
and (S)-enantiomers. The (R)-enantiomer, shown in the figure, has sedative
effects, whereas the (S)-isomer is teratogenic.
CONCLUSION
In conclusion, stereochemistry in natural products is essential
for determining biological activity and enzyme specificity.
Understanding how chiral molecules interact with biological
systems enhances our ability to design effective drugs and
explore biochemical processes, highlighting the precision and
complexity inherent in nature's molecular interactions.
REFERENCES
.
• Introduction to Natural Products and Medicinal Chemistry, David LEMIN. Chiba University 2005
• Chemistry of Plant Natural Products, Sunil Kumar Talapatra · Bani Talapatra
• Consumer Chemistry, A Brief History of Natural Products and Organic Chemistry Chapter 6
• Webster's Revised Unabridged Dictionary (1913). "Natural product". Free Online Dictionary and
C. & G. Merriam Co. A chemical substance produced by a living organism; - a term used
commonly in reference to chemical substances found in nature that have distinctive
pharmacological effects. Such a substance is considered a natural product even if it can be
prepared by total synthesis.
• "All natural". Nature Chemical Biology. 3 (7): 351. July 2007. doi:10.1038/nchembio0707-351.
PMID 17576412. The simplest definition for a natural product is a small molecule that is
produced by a biological source.
• Samuelson G (1999). Drugs of Natural Origin: A Textbook of Pharmacognosy. Taylor & Francis
Ltd,. ISBN 9789186274818.
• National Center for Complementary and Integrative Health (2013-07-13). "Natural Products
Research—Information for Researchers | NCCIH". U.S. Department of Health & Human Services.
Natural products include a large and diverse group of substances from a variety of sources.
They are produced by marine organisms, bacteria, fungi, and plants. The term encompasses
complex extracts from these producers, but also the isolated compounds derived from those
extracts. It also includes vitamins, minerals and probiotics.
• "About Us". Natural Products Foundation. Retrieved 2013-12-07. Natural products are
represented by a wide array of consumer goods that continue to grow in popularity each year.
GROUP MEMBERS
Amponsah Edward 3478522
Bawah Sampson 3480322
Mary Oforiwaa Agyeman 3477422
Tetteh Ebenezer 3485022
Azalete Joseph 3479922
.

THANK YOU
Any Questions?

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